


Curious about Sam- a request for Juggling_Herring

by ZC1996



Category: Supernatural
Genre: F/M, First Time Blow Jobs, first top reader
Language: English
Status: Completed
Published: 2017-07-14
Updated: 2017-07-14
Packaged: 2018-12-02 03:12:13
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,773
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11500566
Author URL: https://archiveofourown.org/users/ZC1996/pseuds/ZC1996
Summary: Can you please do a story where the reader (Sam and Dean's sister) that talked to Sam in his bedroom that night about homework until Sam asked her if she had a bf which she says no. Sam is worried for her since growing up, she has always been shy, even with them. Sam told her that she should go out and mingle and have fun but she didn't want to, saying boys at school just want to have a quick hook up which she's not ready. Curious, she asked Sam what it felt like and Sam ended up explaining to her and she told Sam that she wants to lose it to Sam. Sam wasn't sure at first, but he did it after she begged him. At first, it hurt like hell, like, really hurts but it gets better and she spends the night with him. She's 13 and thanks you!





	Curious about Sam- a request for Juggling_Herring

“You know maybe if you stayed after school and went to study groups you wouldn’t have this much trouble in school.” Sam said as you finish up the last history review question he was helping you with 

“I mean don’t you have a boyfriend or something?” Sam questions leaning against his head board. His hair was longer for the winter going slightly past his shoulders. H He was wearing a dark green long sleeve shirt that showed off a few his muscles. He had dark jeans on with black socks his feet crossed on the bed next to you. You were in your school uniform skirt and a tank top you wore under the scratchy button-down shirt. 

“No, all the boys want girls that they can hook up with in a bathroom stall before football practice. What kind of girl really wants that in life. Besides my friend said it hurt for her.” You blush thinking about all the other things your friend had said how she wished she could do it again every day. 

“You should try and go to a party meet a nice boy and find out for yourself.” Sam chuckled as you put your stuff in your back pack.

“Well, that won’t happen anytime soon.” You scoff rolling your eyes. No party worth going to was one you were invited to.

“Why don’t you just tell me what sex is like. I mean you’ve done it right?” You say leaning back on your hands putting your legs out next to Sam’s.

“Yeah, of course, I’ve had sex _____.” Say said adjusting his feet awkwardly. It wasn’t every day your little sister wanted to talk about such advanced things with an older brother.

“Then tell me what it’s like from a guys perspective.” You persist sitting up to give him your full attention. 

“What exactly do you want to know?” He asked not sure if he really should be talking about this with you.

“What does an orgasm feel like?” You shrug thinking of something off the top of your head.

“It feels like a huge pressure it pushed out of you through your penis.” Sam said carefully making sure not to make it sound as informative as possible.

“How long does it take you to cum?” You asked biting your lip lightly at Sam's slightly shocked face. 

“I usually last 20-30 minutes when I make love, but when I just want to get to it. Like 10-15. Any guy you have that is your age will probably last maybe 5 minutes if you’re lucky in all honest ____.” Sam said adjusting again on the bed moving away from you a bit. 

“Will I cum in 5 minutes?” You asked not liking his answers so far. 

“Truthfully you could if he knew what he was doing, but your partner probably will not and you more than likely will not cum your first time.” Sam said with a smirk seeing your disappointed face. 

“Well, what if I get someone that knows what they are doing? Someone older that will be able to keep me going for a while?” You asked with a blush thinking of the possibilities. 

“Then you could either have the night of your life or you could realize you didn’t want a man for your first time. He won’t be gentle hell he probably won’t remember your name after he is done with you.” Sam warned knowing his words were a little over the top, but he didn’t want to see you getting hurt by someone looking to break a virgin. 

“What if it was someone I knew?” You asked looking at your brother’s firm looking arms outlined by the shirt. 

“Like who?” He asked sitting straighter going through the list of men you knew. 

“Maybe you?” You say sucking your bottom lip into your mouth when you see Sam’s eyes widen for a moment. 

“____ think about what you are asking and who you are asking it too before you say another word.” Sam said sternly looking into your eyes. You stay still staring back running over what it would be like with him. You blush confirming you wanted to do this with him the person you felt most comfortable with in this world. 

“I know you won’t hurt me Sam and you will make it feel amazing.” You said slowly getting up to straddle Sam’s legs. 

“You know this is something you could never tell anyone else.” Sam said putting a hand on your shoulder stopping your slow crawl onto his lap.

“You already said I don’t have a social life. Who would I tell?” You argue back moving to sit on his lap your underwear rubbing against his jeans. 

“It is going to hurt with me ____. I’m a little bigger than most men.” He warned again trying to persuade you away from your decision. You grind against his lap making him moan lightly his hand lightly squeezing your bare thigh. 

“I trust you, Sam. Please take me.” You whisper inches from his face your eyes locked on to his. He leaned in kissing you softly earning another moan from deep in his chest. Your hands spread on his chest feeling the rock-hard muscles flexing as he cupped your butt cheeks through your underwear. He pulled away from your soft lips to yank his shirt over his head. He leaned back on the head board before he pushed your tank top neck line and bra over your breast letting them free. He cupped them gently squeezing lightly, but enough to send pleasure to your groin.

“Oh, that feels good.” You sigh feeling his thumbs swipe over the hard buds before giving each one light kisses. 

“Dean will be home in an hour. Do you want to do this another time?” Sam asked before sucking on each of your nipples playfully. Your hips rocked side to side on his hardening member in his jeans. Your hands running through his long brown hair. 

“No please take me now Sam.” You gasp as he instantly pulls away lifting you off his lap for a moment with a protesting grunt from you. 

“Get undress, but leave the skirt on actually.” Sam said his fingers fumbling with his button and zipper before pulling them down. His penis sprang free curving towards Sam’s stomach already hard. You lick your lips throwing your shirt, bra, and panties in a pile on the floor. Before Sam could say anything, your mouth was wrapped around his red mushroom head. 

“Oh ____.” He gasped one of his hands going to the back of your head. You take him to the back of your throat like they do in porn only to gag immediately. Sam moaned again as you pulled back to going deep liking how he tensed in pleasure every time you did it. 

“Why are you so good at that?” He whispered letting you start to bob faster on his shaft saliva dripping from your inexperienced lips. You pulled back slowly rubbing your hand up and down like they did in the videos. 

“I’ve seen a couple of pornos on Dean’s computer.” You blush ready to put Sam inside of you.

“You dirty girl. Get up here, but face my feet.” Sam directed lifting your skirt to put his cock straight up for you to sink on. You could feel his head poking at your wet entrance.

“When you are ready just sit your pretty pussy down my shaft.” He groaned feeling his head widen your entrance. You pushed him into you slowly feeling his head start to hurt in your walls. 

“AHh! You are big.” You moan out just pushing passed the intense pain through your hymen stopping again with him half way inside. Sam grabbed your hips pushing you down the rest of the way. You moan out leaning forward grabbing on to his legs in front of you.

“So snug on my cock.” Sam hissed out in pleasure his hand lifting your hips up half way to sit you back down quickly. You cried out in more pain unsure when you were supposed to feel the pleasure he was talking about. 

“Use one of your hands to rub your clit ____. Don’t stop until you can't move.” He moaned pulling you back up his shaft while you rubbed the tight nervous awkwardly. At first, it still hurt until a wave of tingles shot through your body from the area. 

“Wow.” You moan letting your hair fall forwards around your face as you rubbed harder. Sam moaned with you moving you faster up and down your shaft. You bucked into him chasing your own crazy need not caring about what your older brother might think. You started to push and pull your hips with Sam his cock head coming out to widen you again. 

“Oh, like that.” You whimper your eyes closing tightly. You hand moved furiously chasing the deep ache bringing it close to the surface with every hard rub. 

“You feel so good.” He grunts also bucking into your hips from underneath adding to the taboo pleasure. 

“I’m gonna-,” You arch your back rubbing faster while your body trembled on top of Sam. 

“Don’t stop!” He roared in his own need quickly turning you both over so that your face was in the pillows. He pulled back to pound that sweet spot inside of you. You cry out as an intense shock ran through your body in crashing waves. He kept a hard pace like before, but with just him in charge, the orgasm skyrocketed making your walls clench him constantly. 

“God damn it ______.” Sam sighed in release pumping harder until he pulled out barely able to stop himself from shooting his cum inside of you. It shot onto the bed in between your legs as he chest laid on your back. 

“I can’t move. That was amazing.” You pant laying on his bed with jelly feeling arms and legs. 

“I’ll carry you to your room Dean will be here soon.” You kind of felt disappointed as Sam picked quickly picked up your clothes. He carried you bridal style to the room across the hall from his room before going back for your backpack. He leaned over giving you a small kiss before turning back to leave.

“My door is open tonight if you want to maybe cuddle tell me how your first time was.” Sam offered with a caring smile before shutting your door letting you sigh happily and a little sore. Not even 10 minutes later Dean came back calling everyone for burgers he had picked up.


End file.
